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Flights from Chicago to Sint Maarten
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Flights from Chicago to Sint Maarten Starting at €105

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip
      • ORD05:00
        8h 6m
        1 stop
        SXM14:06
        Sat, Oct 12|Chicago - Sint Maarten|Spirit Airlines
        €105€194
        46% OFF
        46% OFF
        €194€105
      • ORD18:06
        19h
        1 stop
        SXM14:06
        Tue, Oct 1|Chicago - Sint Maarten|Spirit Airlines
        €114€194
        41% OFF
        41% OFF
        €194€114
      • ORD05:00
        8h 6m
        1 stop
        SXM14:06
        Sat, Oct 26|Chicago - Sint Maarten|Spirit Airlines
        €118€194
        39% OFF
        39% OFF
        €194€118
      • ORD05:20
        7h 46m
        1 stop
        SXM14:06
        Wed, Oct 2|Chicago - Sint Maarten|Spirit Airlines
        €129
        €129
      • ORD05:20
        7h 46m
        1 stop
        SXM14:06
        Sat, Sep 28|Chicago - Sint Maarten|Spirit Airlines
        €130
        €130
      • ORD05:00
        8h 6m
        1 stop
        SXM15:06
        Mon, Nov 4|Chicago - Sint Maarten|Spirit Airlines
        €135
        €135
      • ORD05:00
        8h 6m
        1 stop
        SXM14:06
        Wed, Oct 23|Chicago - Sint Maarten|Spirit Airlines
        €136
        €136
      • ORD05:00
        8h 6m
        1 stop
        SXM14:06
        Fri, Oct 25|Chicago - Sint Maarten|Spirit Airlines
        €136
        €136
      • ORD05:00
        8h 6m
        1 stop
        SXM14:06
        Mon, Oct 21|Chicago - Sint Maarten|Spirit Airlines
        €137
        €137
      • ORD05:20
        7h 46m
        1 stop
        SXM14:06
        Mon, Sep 30|Chicago - Sint Maarten|Spirit Airlines
        €138
        €138
      • CHI13:00
        3h 5m
        Direct
        SXM14:00
        Wed, Sep 25|Chicago - Sint Maarten|Spirit Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Find the best time to fly from Chicago to Sint Maarten

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Airlines Flying from Chicago to Sint Maarten

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

Frontier Airlines
From €86
Spirit Airlines
From €105
American Airlines
From €118
Jetblue Airways
From €140
Delta Air Lines
From €150
United Airlines
From €180
Air Canada
From €212
Porter Airlines
From €229
Copa Airlines
From €270
Air Transat
From €272
ANA airlines

Find more flights and airlines

Alternative Routes from Chicago to Sint Maarten

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from Chicago to Sint Maarten.

  • Cheapest
    Frontier Airlines
    MDW
    20:03
    19h 31m
    2 transfer
    SXM
    16:34
    Midway International Airport - Princess Juliana International Airport
    Fri, Oct 4Frontier Airlines
    €86
  • Spirit Airlines
    ORD
    05:00
    8h 6m
    1 transfer
    SXM
    14:06
    O'Hare International Airport - Princess Juliana International Airport
    Sat, Oct 12Spirit Airlines
    €105
  • Spirit Airlines
    ORD
    05:00
    8h 6m
    1 transfer
    SXM
    14:06
    O'Hare International Airport - Princess Juliana International Airport
    Sat, Oct 12Spirit Airlines
    €105
    Find More Flights

How do I find the cheapest flights?

  • When are flight tickets from Chicago (CHI) to Sint Maarten (SXM) the cheapest?

    Airlines adjust prices for flights from Chicago to Sint Maarten based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Chicago (CHI) to Sint Maarten (SXM) cost?

    According to Trip.com's data, the lowest price is around €469.

How to find a cheap flight from Chicago to Sint Maarten

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Sint Maarten. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information from Chicago to Sint Maarten

Cheapest nonstop flight price

€104

Cheapest round-trip ticket price

€519

Off-season for travel

October

Peak season for travel

December

Flight distance

3,524.79km

Popular airline

American Airlines

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